The invention relates to novel benzenesulfonamide compounds, agriculturally suitable compositions containing them, and their method-of-use as general and selective preemergent and postemergent herbicides.
European Patent Application (EP-A) No. 83,975 (published July 20, 1983) discloses herbicidal benzenesulfonamides of formula ##STR1## wherein Q is selected from various five or six-membered aromatic or partially unsaturated heterocyclic rings containing 2 or 3 heteroatoms selected from O, S or NR.
EP-A-85,476 (published Aug. 10, 1983) discloses herbicidal benzenesulfonamides of formulae ##STR2## wherein Q is selected from various 5-membered aromatic heterocycles, and their dihydro and tetrahydro analogs, which contain one heteroatom selected from O, S or NR, or Q is a saturated or partially unsaturated 6-membered ring containing one heteroatom selected from O or S; and
Q.sup.1 is a 6-membered aromatic heterocycle containing one to three N atoms. PA0 R.sub.2 is H or C.sub.1 -C.sub.3 alkyl; PA0 R.sub.3 is H or CH.sub.3 ; PA0 R.sub.4 is H or CH.sub.3 ; and PA0 A is a pyrimidinyl or triazinyl heterocyclic ring. PA0 Q is ##STR9## G is CH.sub.2, CH.sub.2 CH.sub.2, O, S, NH, NCH.sub.3 or CH.dbd.CH; G.sub.1 is CH.sub.2, CH.sub.2 CH.sub.2 or CH.dbd.CH; PA0 J is CH.sub.2, C.dbd.O, S(O).sub.m, O, NH, NCH.sub.3, CHOH, CHOCH.sub.3, CH(CH.sub.3) or C(CH.sub.3)OH; PA0 J.sub.1 is CH.sub.2, C.dbd.O or SO.sub.2 ; PA0 n and n.sub.1 are independently 0 or 1; PA0 m is 0, 1 or 2; PA0 E is a bridge of 3 or 4 atoms containing 0 to 2 heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen, wherein 1 atom of sulfur may take the form of SO or SO.sub.2, said bridge also containing 1 to 4 atoms of carbon wherein 1 atom of carbon may take the form of C.dbd.O, said bridge together with two attachment sites forming a non-aromatic heterocyclic or carbocyclic ring optionally substituted by 1 to 3 substituent groups selected from the group L, or E is a bridge of 3 or 4 atoms containing 0-1 heteroatoms of oxygen or sulfur and 0-3 heteroatoms of nigrogen, said bridge also containing 0-4 atoms of carbon, said bridge together with two attachment sites forming an aromatic heterocyclic or carbocyclic ring optionally substituted by 1 to 3 substituents selected from the group L, with the proviso that when E contains two oxygen atoms or two sulfur atoms said atoms must be separated by at least one atom of carbon and that oxygen and sulfur are only linked to each other if the sulfur is in the form of SO or SO.sub.2 ; PA0 L is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.2 -C.sub.8 alkoxyalkoxy, halogen, N(CH.sub.3).sub.2, cyano, nitro, phenyl or phenyl substituted with C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, NO.sub.2, C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl or C.sub.1 -C.sub.3 alkylsulfonyl; PA0 R is H or CH.sub.3 ; PA0 R.sub.1 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 haloalkyl, halogen, nitro, C.sub.1 -C.sub.3 alkoxy, SO.sub.2 NR.sup.I R.sup.II, C.sub.1 -C.sub.3 alkylthio, C.sub.1 -C.sub.3 alkylsulfinyl, C.sub.1 -C.sub.3 alkylsulfonyl, CO.sub.2 R.sup.III or NR.sub.a R.sub.b ; PA0 R.sup.I is H, C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.3 cyanoalkyl, methoxy or ethoxy; PA0 R.sup.II is H, C.sub.1 -C.sub.4 alkyl or C.sub.3 -C.sub.4 alkenyl; or PA0 R.sup.I and R.sup.II may be taken together as --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 -- or --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --; PA0 R.sup.III is C.sub.1 -C.sub.4 alkyl, C.sub.3 --C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl, C.sub.2 -C.sub.4 haloalkyl, C.sub.1 -C.sub.3 cyanoalkyl, C.sub.5 -C.sub.6 cycloalkyl, C.sub.4 -C.sub.7 cycloalkylalkyl or C.sub.2 -C.sub.4 alkoxyalkyl; PA0 R.sub.a and R.sub.b are independently H or C.sub.1 -C.sub.2 alkyl; PA0 A is ##STR10## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA0 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.3 -C.sub.5 cycloalkyl, C.sub.2 -C.sub.4 alkynyl, N(OCH.sub.3)CH.sub.3, ##STR11## p is 2 or 3; L.sub.1 and L.sub.2 are independently O or S; PA0 R.sub.2 and R.sub.3 are independently C.sub.1 -C.sub.2 alkyl; PA0 R.sub.4 is H or CH.sub.3 ; PA0 Z is CH or N; PA0 Y.sub.1 is O or CH.sub.2 ; PA0 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA0 Y.sub.2 is H or CH.sub.3 ; PA0 X.sub.2 is CH.sub.3, OCH.sub.3 or SCH.sub.3 ; PA0 Y.sub.3 is CH.sub.3, CH.sub.2 CH.sub.3 or CH.sub.2 CF.sub.3 ; PA0 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA0 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA0 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA0 (a) when X is Cl, F, Br or I, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, N(OCH.sub.3)CH.sub.3, NHCH.sub.3, N(CH.sub.3).sub.2 or OCF.sub.2 H; PA0 (b) when X or Y is OCF.sub.2 H, then Z is CH; PA0 (c) n and n.sub.1 cannot simultaneously be O; PA0 (d) when G or G.sub.1 is CH.sub.2 CH.sub.2 or CH.dbd.CH, then n is 0; PA0 (e) when Q is Q.sub.1 and n is 1, then E must contain at least one heteroatom selected from oxygen, sulfur or nitrogen; and PA0 (f) when W is S, then A is A-1, R is H, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR12## PA0 (1) Compounds of Formula I where W is O; G and G.sub.1 are CH.sub.2, CH.sub.2 CH.sub.2 or CH.dbd.CH; J is CO, SO.sub.2 or CH.sub.2 ; R is H; X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, F, Br, I, OCF.sub.2 H, CH.sub.2 F, OCH.sub.2 CH.sub.2 F, OCH.sub.2 CHF.sub.2, OCH.sub.2 CF.sub.3, CF.sub.3, CH.sub.2 Cl or CH.sub.2 Br; Y is H, CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, NHCH.sub.3, N(OCH.sub.3)CH.sub.3, N(CH.sub.3).sub.2, CH.sub.2 CH.sub.3, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, CH.sub.2 OCH.sub.2 CH.sub.3, OCH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 SCH.sub.3, ##STR13## OCF.sub.2 H, SCF.sub.2 H, cyclopropyl, C.tbd.CH or or C.tbd.CCH.sub.3 ; (2) Compounds of Preferred 1 where R.sub.1 is H, CH.sub.3, halogen, OCH.sub.3, SCH.sub.3 or SO.sub.2 CH.sub.3 ; A is A-1; and L is halogen, CH.sub.3, OCH.sub.3 or phenyl. PA0 (3) Compounds of Preferred 2 where Q is ##STR14## R.sub.5 is H or CH.sub.3 ; R.sub.6 is H, CH.sub.3 or phenyl; PA0 R.sub.7 is H or CH.sub.3 ; PA0 R.sub.8 is H or CH.sub.3 ; PA0 R.sub.9 is H, CH.sub.3 or phenyl; PA0 R.sub.10 is H or CH.sub.3 ; PA0 R.sub.11 is SCH.sub.3, OCH.sub.3, N(CH.sub.3).sub.2 or CH.sub.3 ; PA0 R.sub.12 is H or CH.sub.3 ; PA0 R.sub.13 is H, CH.sub.3, OCH.sub.3 or SCH.sub.3 ; and PA0 R.sub.14 is H, Cl, Br, F, CH.sub.3, OCH.sub.3 or NO.sub.2. PA0 (4) Compounds of Preferred 3 where X is CH.sub.3, OCH.sub.3, OCH.sub.2 CH.sub.3, Cl, OCF.sub.2 H or OCH.sub.2 CF.sub.3 ; and Y is CH.sub.3, OCH.sub.3, CH.sub.2 CH.sub.3, CH.sub.2 OCH.sub.3, NHCH.sub.3 or CH(OCH.sub.3).sub.2. PA0 (5) Compounds of Preferred 4 where n is 0. PA0 (6) Compounds of Preferred 4 where n.sub.1 is 0. PA0 (7) Compounds of Preferred 5 where Q is Q.sub.1 -4, Q.sub.1 -6, Q.sub.1 -17, Q.sub.1 -18, Q.sub.1 -19, Q.sub.1 -21, Q.sub.1 -22, Q.sub.1 -23, Q.sub.2 -1 or Q.sub.3 -1. PA0 (8) Compounds of Preferred 6 where Q is Q.sub.1 -2, Q.sub.1 -3 or Q.sub.1 -14. PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-1-phenyl-1H-[1]benzothieno[3 ,2-C]pyrazole-5-sulfonamide, 4,4-dioxide, m.p. 243.degree.-248.degree. C. PA0 4,5-dihydro-N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]naphth[2,1-D]isox azole-9-sulfonamide, m.p. 189.degree.-192.degree. C.(d). PA0 4,5-dihydro-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]naphth[2,1-D ]isoxazole-9-sulfonamide, m.p. 186.degree.-189.degree. C. PA0 4,5-dihydro-N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]naphth[2,1-D ]isoxazole-9-sulfonamide, m.p. 147.degree.-150.degree. C.
South African Patent Application No. 83/8416 (published May 12, 1984) discloses herbicidal benzenesulfonamides of formula ##STR3## wherein A is an unsaturated or only partially saturated 5- or 6-membered heterocyclic ring system which is bonded through a carbon atom and contains 1, 2 or 3 heteroatoms.
EP-A-79,683 (published May 25, 1983) discloses herbicidal benzenesulfonamides including those of general Formulae I and II: ##STR4## wherein Q is O, S or SO.sub.2 ;
EP-A-107,979 (published May 9, 1984) teaches herbicidal sulfonamides of formula ##STR5## where J is, among other values, ##STR6## wherein n is 0, 1 or 2.
EP-A-82,681 (published June 29, 1983) discloses herbicidal indane, 1,3-benzodioxole and 1,4-benzodioxanesulfonylureas.
South African Patent Application No. 83/5165 (published Jan. 16, 1984) discloses herbicidal sulfonylureas of the general structure shown below: ##STR7## wherein A is an unsubstituted or substituted bridge of 3 or 4 atoms which contains 1 or 2 oxygen, sulfur or nitrogen atoms and, together with the linking carbon atom, forms a non-aromatic 5- or 6-membered heterocyclic ring system, with the proviso that two oxygen atoms are separated by at least one carbon atom and that oxygen and sulfur atoms are only linked to each other if the sulfur atom takes the form of the --SO-- or SO.sub.2 -- group.